Benzoyl chloride → 6-Oxobicyclo[3.2.0]heptan-2-yl benzoate

HRID 642745

Reaction equation

HRID 642745 reaction equation
[OH:1][CH:2]1[CH2:8][CH2:7][CH:6]2[CH:3]1[CH2:4][C:5]2=[O:9].CCN(CC)CC.[C:17](Cl)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[C:17]([O:1][CH:2]1[CH2:8][CH2:7][CH:6]2[CH:3]1[CH2:4][C:5]2=[O:9])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 134438072-Hydroxybicyclo[3.2.0]heptan-6-one

Product 1

HCID 592595756-Oxobicyclo[3.2.0]heptan-2-yl benzoateYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of compound 1G (1.9 g, 15.1 mmol) in CH2Cl2 (10 mL) at 0° C. under nitrogen were added Et3N (3.1 mL, 22.2 mmol) and benzoyl chloride (2.33 g, 16.6 mmol). The reaction was stirred at 0° C. for 60 min and RT for 30 min, then quenched with water. The product was extracted with CH2Cl2, the organics were washed with saturated aqueous NaHCO3, dried over Na2SO4, and concentrated. Purification by silica gel chromatography (5% EtOAc in hexanes) provide the title compound (3 g).

Workup

  1. customquenched with water
  2. extractionThe product was extracted with CH2Cl2
  3. washthe organics were washed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-702fd5351b1f45cbbfb37422ed9dc037
Source dataset
uspto-grants-2010_04
Patent number
US07696241B2

Linked notes

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